Premium
Stereoselective synthesis of alcohols, XXII. E/Z ‐selectivity on addition of α‐substituted allylboronates to aldehydes
Author(s) -
Hoffmann Reinhard W.,
Landmann Bernd
Publication year - 1986
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19861190324
Subject(s) - chemistry , stereoselectivity , selectivity , medicinal chemistry , stereochemistry , organic chemistry , catalysis
α‐Heterosubstituted allylboronates 7 are prepared. Addition of 7 to aldehydes results in E/Z ‐isomeric homoallyl alcohols 13 and 14 . The reasons for the predominant formation of the Z ‐isomer 14 are discussed. The Z ‐bromo olefins 16 and 20 obtained in this way serve as starting point for chain extension or formation of δ‐lactones 21 .